How to explore one's career path: Practical thoughts on stepping outside the comfort zone

What do you dream of accomplishing one day? For me, a decade ago, I imagined living in a nice condo in Toronto, Canada. Fast forward to the present: I have been living that dream for several years, and I basically take it for granted now, but to the teenage me, that seemed such a distant fairytale dream.

At each point in life, I had dreams and “one day” goals. “One day I’ll be a successful data scientist” was one of them. These dreams are scary, and the journey from the inception of the dream, to when it comes true, is often a black box.

I look back on the dreams that I had no idea how I could carry out, yet, somehow, I now can proudly say I have accomplished. In fact, this pattern has repeated itself many times.

Examples include:

Graduate university despite failing 3 courses, while volunteering 10+ hours per week each school term. Developed a video game while a student in economics, and also while working full time. Took a year longer than everyone to finish my master’s degree, having prioritized a job interview in Paris, France over a final exam. Seek employment in data science, where I had no educational “credentials”.

I list these past dreams of mine, not to brag, but to illustrate that even the dreams that seem unrelated to career per se, ended up having a lot to do with how I figured out my career path. In typical fashion of this blog, I’ll outline the common, reproducible patterns that helped me be successful in those endeavors.

• Do the difficult thing
• If you have overcome difficulties in the past, new, difficult things are relatively easy
• Three things I tell myself when facing difficulties

Do the difficult thing

Continuing the story at the beginning of this article, I came to Canada with two suitcases, alone, in 2012. The very last time I had been in Canada was 2002. I slept in the airport to save money, because the University of Waterloo’s free shuttle bus came the next day. Some weeks after, I took a bus to downtown Toronto - it was my very first time seeing Toronto. I looked at the tall office buildings and condos and I thought to myself: “Some day I will work here, and I’ll live in one of these buildings.”

At the time I had barely started university, much less having a degree that could help me get a full time job to live in a condo. That was a lot of steps to make the dream come true! There were many times in between, where I felt that it would be impossible, that “I can’t do it”.

For example, I failed 3 courses in university, but I still kept going. The mental strength came from anchoring it back to those first few difficult days when I landed back in Canada: “I have made it this far, what’s redoing this course compared to that?”

There were many other paths of less resistance: I could transfer schools, or stop spending time volunteering, or try to graduate with the bare minimum “Cs get degrees” (C as in the letter grade).

However, I chose the difficult path, and earned grades high enough to get the professors of two most difficult upper year courses to write me recommendation letters and got into the University of Toronto for grad school.

I believe simply refusing those paths of least resistance opened the doors for me to enter data science, which is competitive. If I ever explore other career paths, I can reproduce this process, and I share it in the hopes that you can, too, with your own career path and dreams.

If you have overcome difficulties in the past, new, difficult things are relatively easy

Now, I’ve sometimes wondered where my confidence then came from. Something difficult like sleeping overnight in the airport doesn’t seem directly comparable to studying for exams. But let’s set that aside for a moment and think in broader strokes: everyone, including you has overcome something difficult, something that you thought was the most difficult thing you have ever done.

Given that logic, you are able to do anything else, since it will be easier than what you have survived already. It is important to internalize that sense of confidence and agency. When I was applying to my first full time role, I had many rejections, of course, and I thought, “Well, I survived University of Toronto and University of Waterloo, so how difficult can finding a job be?”

The point I make about internalization is that, I had to believe that it was me that was the common denominator, and not that those degrees were some sort of golden ticket to any job.

One should not rely on value bestowed by a third party: phrasing it like “Employers must hire me because of [degree]”, or “Why aren’t employers hiring me, even if I have [degree]?”. But rather, it is more helpful to use a first person phrasing: “I can overcome difficult job searches because I have survived [degree]”. No one owes me anything because of the school I went to, or the side project that I did.

Therefore, when it came to exploring my full time career, I neither felt limited nor, on the other hand, entitled, because of my academic degrees. “I can enter data science if I want to, even if I have economics (literally Bachelor and Master of Arts) degrees. Those degrees were both from schools notorious for being difficult!” “I can enter game development if I so choose, because I have been making games as a hobby, which wasn’t easy.”

My interests might not have been a typical career path compared to average, sure, but this mindset helped me counter impostor syndrome by anchoring the difficulty of the career path to hardships I have survived in the past. It doesn’t matter if the past hardship, like my airport sleeping example, isn’t 100% directly related to the difficulty on hand, as long as it invokes a relevant confidence in yourself.

For each of the challenges I’ve faced and then overcome, choosing the difficult thing has helped me, and I hope it can speak to you. Think about your past experiences: You must have overcome so much already compared to your comfort zone years ago! Use the examples in your past to help smash your current comfort zone.

Three things I tell myself when facing difficulties

1. Difficult things aren’t as difficult as they seem.
2. If you have accomplished something difficult in the past, new, difficult things are relatively easy.
3. Say “yes!”, not “I want to, but…”. Avoid saying “I can’t” as a knee jerk response to challenges.

Finally, here are some examples where this mindset has helped me through difficult and dark times, where honestly I had been close to giving up.

• Getting into data science from a less represented educational background: “I have gotten through two notoriously difficult universities! I know that I have what it takes to enter this new field.” (Note: it turns out that there are many people with economics background in the data science and machine learning field.)

• Doing well in a full day job interview in Paris, France, even with fatigue from timezone difference (their 9 am being Canada’s 3 am): “One time I only had 3 hours to pack 2 months’ worth of clothes and get to the airport, immediately after a final exam, and I made it! I’ve survived that, a little jet lag isn’t going to affect my interview!”

• Working on a video game during weekends while working full time: “When I was in school I volunteered 10+ hours every week for ten consecutive school terms, and still (eventually) earned great grades. I have the time management skills and discipline to perform well at work on weekdays, and also my own project during the weekend.”

I acknowledge that some people don’t have some luxuries I had, such as leadership positions in clubs and volunteering as a student - the same time might be spent working part-time jobs. The logic here is the same - they were able to focus on their “full-time” student responsibilities, while succeeding in working on other obligations.

With your personal example of a hardship you have overcome, and the experience of managing your time and building that discipline, anything in your career path surely is within your abilities as well, no matter how difficult it seems.

I hope that by sharing how I accomplished many of my dreams and explored my career path by stepping outside of my comfort zone, drawing on confidence from past hardships I survived, can resonate with you. Here’s to your big dreams!